He’s also been Captain of USS Jeopardy for almost 30 years. And with the 50th anniversary of said quiz show coming up this Sunday, we’re taking a look back at the very best (and worst) of Alex Trebek’s style.

Every Wednesday from here on out, we’re giving you a piece of our minds. Actually, more like five pieces. It’s a chance to get a deeper look into what makes the minds behind Kempt tick—you know, beyond the usual Internet handsomeness we’re serving up daily. So welcome to our most personal weekly feature: The Kempt Five.

Because even though summer only officially started last Friday, we’ve been talking about it since early May—and the last thing on our minds in the sweltering heat we’re all now starting to feel is fall tweeds.

It’s this “trickiness,” among other things, that led the gents at two of our big three men’s rags to the same decision years ago: July wasn’t worth the hassle of its own issue, so they tacked it onto the end of June’s. Which has given us the rare opportunity to look past those dusty old stalwarts to a few of the other menswear mags out there.

And heralding this great news has been one of the most stylish ad campaigns we’ve seen in a while. (Not that we’d expect anything less.)

We’re especially digging the chalky illustrations that look like they could’ve been borrowed from the boardroom easel of Draper’s latest pitch. Which isn’t far off, considering the artwork was done by a real-deal advertising illustrator from the 1960s: Brian Sanders, who actually lived the life and lives to tell the tale. AMC recently sat down with Sanders to hear some of it and got a look at the illustrations in their various stages of production—which reveals some interesting details, like the inspiration photo collage depicting Don Draper walking past himself (in the lighter gray suit).